Abstract
A wide variety of novel non-hygroscopic N-oxide tetraphenylborate salts were synthesized and evaluated as co-oxidants in the Ley–Griffith (TPAP) oxidation of benzylic and allylic alcohols under non-anhydrous conditions. The novel DABCOO·TPB (2:1) salt was herein unearthed as a viable competitor to the first-generation NMO·TPB (2:1) salt, but more importantly gave increased performance under oxidative competition. X-ray crystal structure analysis and NMR spectroscopy revealed that depending on the crystallization conditions 1:1, 2:1 or 3:2 N-oxide–tetraphenylborate salts could be formed.
Original language | English |
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Pages (from-to) | 3401-3407 |
Number of pages | 7 |
Journal | European Journal of Organic Chemistry |
Volume | 2016 |
Issue number | 20 |
DOIs | |
Publication status | Published - Jul 2016 |
Externally published | Yes |
Keywords
- Alcohols
- Oxidation
- Aldehydes
- Ley-Griffith reaction
- N-Oxide salts
- TPAP